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ES2544819T3 - Process for the production of precursors of vitamin D phosphine oxide - Google Patents

Process for the production of precursors of vitamin D phosphine oxide Download PDF

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Publication number
ES2544819T3
ES2544819T3 ES08762721.2T ES08762721T ES2544819T3 ES 2544819 T3 ES2544819 T3 ES 2544819T3 ES 08762721 T ES08762721 T ES 08762721T ES 2544819 T3 ES2544819 T3 ES 2544819T3
Authority
ES
Spain
Prior art keywords
tetra
butylammonium
formula
phosphine oxide
bromide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
ES08762721.2T
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Spanish (es)
Inventor
Uttam Saha
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
OPKO IP HOLDINGS II Inc
Original Assignee
OPKO IP HOLDINGS II Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by OPKO IP HOLDINGS II Inc filed Critical OPKO IP HOLDINGS II Inc
Application granted granted Critical
Publication of ES2544819T3 publication Critical patent/ES2544819T3/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5316—Unsaturated acyclic phosphine oxides or thioxides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

Un proceso para producir un compuesto de fórmula:**Fórmula** que comprende hacer reaccionar un compuesto de fórmula:**Fórmula** con óxido de difenil fosfina usando una mezcla de reacción de fase binaria que comprende óxido de difenil fosfina en un solvente orgánico, una solución acuosa básica, y un catalizador de transferencia de fase, para obtener el compuesto de fórmula 1, en donde Ph es fenilo, X1 y X2 son ambos hidrógeno o X1 y X2 tomados juntos son CH2, R1 es un grupo protector, R2 es flúor, hidrógeno, u OR3, en donde R3 es un grupo protector, y la línea ondulada representa un enlace que resulta del doble enlace adyacente que está en la configuración ya sea E o Z y, en donde la etapa de reacción se realiza a una temperatura en un intervalo de aproximadamente 0 °C a aproximadamente 40 °C.A process for producing a compound of formula: ** Formula ** comprising reacting a compound of formula: ** Formula ** with diphenyl phosphine oxide using a binary phase reaction mixture comprising diphenyl phosphine oxide in a solvent organic, a basic aqueous solution, and a phase transfer catalyst, to obtain the compound of formula 1, wherein Ph is phenyl, X1 and X2 are both hydrogen or X1 and X2 taken together are CH2, R1 is a protective group, R2 is fluorine, hydrogen, or OR3, where R3 is a protective group, and the wavy line represents a bond that results from the adjacent double bond that is in the configuration either E or Z and, where the reaction stage is performed at a temperature in a range of about 0 ° C to about 40 ° C.

Description

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E08762721 E08762721

07-08-2015 07-08-2015

Nitrato de tetraetilamonio Tetraethylammonium Nitrate

Perclorato de tetraetilamonio Tetraethylammonium perchlorate

Tetrafluoroborato de tetraetilamonio Tetraethylammonium tetrafluoroborate

Bromuro de metiltri-n-butilamonio Methyltri-n-butylammonium bromide

Cloruro de metiltri-n-butilamonio Methyltri-n-Butylammonium Chloride

Bromuro de (1-decil)trimetilamonio (1-decyl) trimethylammonium bromide

Bromuro de benciltrietilamonio Benzyltriethylammonium bromide

Cloruro de benciltrietilamonio Benzyltriethylammonium Chloride

Hidróxido de benciltrietilamonio Benzyltriethylammonium Hydroxide

Tetrafluoroborato de benciltrietilamonio Benzyltriethylammonium tetrafluoroborate

Cloruro de (1-dodecil)trimetilamonio (1-Dodecyl) Trimethylammonium Chloride

Bromuro de (1-dodecil)trimetilamonio (1-dodecyl) trimethylammonium bromide

Cloruro de benciltri-n-propilamonio Benzyltri-n-propylammonium chloride

Acetato de tetra-n-butilamonio Tetra-n-Butylammonium Acetate

Acetato de tetra-n-butilamonio Tetra-n-Butylammonium Acetate

Bromuro de tetra-n-butilamonio Tetra-n-Butylammonium Bromide

Cloruro de tetra-n-butilamonio Tetra-n-Butylammonium Chloride

Cloruro de tetra-n-butilamonio Tetra-n-Butylammonium Chloride

Hexafluoro-fosfato de tetra-n-butilamonio Tetra-n-Butylammonium Hexafluoro Phosphate

Tetra-n-butilamonio hidrogenosulfato Tetra-n-Butylammonium Hydrogen Sulfate

Hidróxido de tetra-n-butilamonio Tetra-n-Butylammonium Hydroxide

Hidróxido de tetra-n-butilamonio Tetra-n-Butylammonium Hydroxide

Hidróxido de tetra-n-butilamonio Tetra-n-Butylammonium Hydroxide

Hidróxido de tetra-n-butilamonio Tetra-n-Butylammonium Hydroxide

Yoduro de tetra-n-butilamonio Tetra-n-Butylammonium iodide

Nitrato de tetra-n-butilamonio Tetra-n-Butylammonium Nitrate

Perclorato de tetra-n-butilamonio Tetra-n-Butylammonium Perchlorate

Perclorato de tetra-n-butilamonio Tetra-n-Butylammonium Perchlorate

Fosfato de tetra-n-butilamonio Tetra-n-Butylammonium Phosphate

Sulfato de tetra-n-butilamonio Tetra-n-Butylammonium Sulfate

Tetra-n-butilamoniotrifluorometano sulfato Tetra-n-Butylammoniotrifluoromethane Sulfate

Hidróxido de tetra-n-propilamonio Tetra-n-Propylammonium Hydroxide

Yoduro de tetra-n-propilamonio Tetra-n-propylammonium iodide

Yoduro de feniltrietilamonio Phenyltriethylammonium iodide

Bromuro de (1-tetradecil)trimetilamonio (1-tetradecyl) trimethylammonium bromide

Cloruro de (1-tetradecil)trimetilamonio (1-tetradecyl) trimethylammonium chloride

Bromuro de (1-tetradecil)trimetilamonio (1-tetradecyl) trimethylammonium bromide

Bromuro de (1-hexadecil)trimetilamonio (1-hexadecyl) trimethylammonium bromide

Etil(1-hexadecil)dimetilamonio Ethyl (1-hexadecyl) dimethylammonium

Yoduro de tetra-n-pentilamonio Tetra-n-pentyl ammonium iodide

Bromuro de benciltri-n-butilamonio Benzyltri-n-butylammonium bromide

Cloruro de benciltri-n-butilamonio Benzyltri-n-Butylammonium Chloride

Yoduro de benciltri-n-butilamonio Benzyltri-n-butylammonium iodide

Bromuro de (1-hexadecil)piridino monohidrato (1-Hexadecyl) pyridine monohydrate bromide

Cloruro de (1-hexadecil)piridino monohidrato (1-Hexadecyl) pyridine monohydrate chloride

Bromuro de di-n-decildimetilamonio Di-n-decyldimethylammonium bromide

Bromuro de tetra-n-hexilamonio Tetra-n-Hexyl ammonium bromide

Tetra-n-hexilamonio hidrogenosulfato Tetra-n-hexylammonium hydrogen sulfate

Yoduro de tetra-n-hexilamonio Tetra-n-hexylammonium iodide

Perclorato de tetra-n-hexilamonio Tetra-n-hexylammonium perchlorate

Bromuro de di-n-dodecildimetilamonio Di-n-dodecyldimethylammonium bromide

Bromuro de tetra-n-heptilamonio Tetra-n-Heptylammonium Bromide

Yoduro de tetra-n-heptilamonio Tetra-n-heptylammonium iodide

Bromuro de tetra-n-octilamonio Tetra-n-octylammonium bromide

Cloruro de dimetildiestearilamonio Dimethyldiestearylammonium chloride

Yoduro de tetra-n-dodecilamonio Tetra-n-dodecylammonium iodide

Bromuro de tetraoctadecilamonio Tetraoctadecylammonium bromide

6 6

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Claims (1)

imagen1image 1 imagen2image2
ES08762721.2T 2007-05-30 2008-05-23 Process for the production of precursors of vitamin D phosphine oxide Active ES2544819T3 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US94086607P 2007-05-30 2007-05-30
US940866P 2007-05-30
PCT/IB2008/001321 WO2008146130A1 (en) 2007-05-30 2008-05-23 Process for producing phosphine oxide vitamin d precursors

Publications (1)

Publication Number Publication Date
ES2544819T3 true ES2544819T3 (en) 2015-09-04

Family

ID=40074615

Family Applications (1)

Application Number Title Priority Date Filing Date
ES08762721.2T Active ES2544819T3 (en) 2007-05-30 2008-05-23 Process for the production of precursors of vitamin D phosphine oxide

Country Status (7)

Country Link
US (1) US8039676B2 (en)
EP (1) EP2167516B1 (en)
JP (1) JP5480131B2 (en)
CN (1) CN101754971A (en)
CA (1) CA2688083C (en)
ES (1) ES2544819T3 (en)
WO (1) WO2008146130A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2603519B1 (en) * 1986-07-29 1989-03-10 Nergeco Sa PROCESS FOR THE MANUFACTURE OF FLEXIBLE CURTAINS OF ANY SIZE AND DEVICE FOR IMPLEMENTING SAME
CN111659471B (en) * 2020-06-18 2023-06-02 河北威远生物化工有限公司 Catalyst for synthesizing emamectin benzoate intermediate imine compound and application thereof

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3992432A (en) * 1967-04-05 1976-11-16 Continental Oil Company Phase transfer catalysis of heterogeneous reactions by quaternary salts
FR2472575B1 (en) * 1979-12-28 1985-10-04 Poudres & Explosifs Ste Nale PROCESS FOR THE SYNTHESIS OF TERTIARY PHOSPHINE OXIDES AND NOVEL TERTIARY PHOSPHINES OXIDES
GB2198725B (en) * 1986-11-05 1991-01-16 Alter Sa Use of a series of quaternary ammonium salts as phase-transfer catalysts
US5001250A (en) * 1989-05-30 1991-03-19 Occidental Chemical Corporation Purification of bidentate organophosphorous extractants
AU650751B2 (en) * 1991-05-28 1994-06-30 Wisconsin Alumni Research Foundation Novel synthesis of 19-nor vitamin D compounds
SG70009A1 (en) 1996-05-23 2000-01-25 Hoffmann La Roche Vitamin d3 analogs
US6603030B1 (en) * 1999-04-22 2003-08-05 Hoffman-La Roche Inc. Process for producing phosphineoxide vitamin D precursors
US6331642B1 (en) * 1999-07-12 2001-12-18 Hoffmann-La Roche Inc. Vitamin D3 analogs
WO2006019169A1 (en) * 2004-08-17 2006-02-23 Teijin Pharma Limited 3-epivitamin d3 derivative and therapeutic agent containing the same
WO2007022433A2 (en) * 2005-08-18 2007-02-22 Bioxell S.P.A. SYNTHESIS OF 1α-FLUORO-25-HYDROXY-16-23E-DIENE-26,27-BISHOMO-20-EPI-CHOLECALCIFEROL
US20100069339A1 (en) * 2006-10-13 2010-03-18 Bioxell S.P.A. Novel method of treatment of male sub-fertility

Also Published As

Publication number Publication date
US8039676B2 (en) 2011-10-18
US20080300427A1 (en) 2008-12-04
CA2688083C (en) 2015-07-07
JP2010528099A (en) 2010-08-19
JP5480131B2 (en) 2014-04-23
EP2167516A1 (en) 2010-03-31
EP2167516A4 (en) 2012-04-11
WO2008146130A1 (en) 2008-12-04
CA2688083A1 (en) 2008-12-04
CN101754971A (en) 2010-06-23
EP2167516B1 (en) 2015-07-22

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